It's not often that a property comes along that feels this distinctive--and even less often that you can find this much space and character right on Main Street in downtown Jonesborough. This 3,003-square-foot penthouse condo offers three bedrooms, two full baths, and a setting that puts you right in the heart of one of Tennessee's most historic towns. The character of the original building is everywhere you look, from the tall ceilings and exposed brick walls to the texture of the original plaster and beautiful hardwood floors. Large windows bring in natural light and offer views over quaint downtown Jonesborough, creating a home that feels connected to everything happening just outside your door. The layout is both spacious and flexible. The eat-in kitchen features tall ceilings and opens to a large great room with plenty of room for both living and dining. A wet bar adds a nice touch for entertaining, while the open arrangement allows the great room to be furnished in a variety of ways to suit your lifestyle--whether you want a comfortable gathering space, a dedicated dining area, a home office, or a combination of uses. An open back deck extends the living space outdoors and provides a private spot to enjoy the fresh air. The primary suite offers its own comfortable retreat with a double vanity, while two additional bedrooms provide flexibility for guests, family, or office space. And the building itself has a story worth knowing. Known historically as Lampson Hall, it has stood on the courthouse square since about 1873 and, for much of its history, was a gathering place for the community. The third floor once served as the town's hall, hosting plays, vaudeville, and traveling companies passing through Jonesborough. The lower floors housed retail businesses, and when Washington County outgrew its courthouse, the county court met here until the new courthouse was completed in 1913. For decades, the ground floor was home to the Hoss and McCall clothing store, giving the building another name by which it is remembered today. The entire building was renovated in 2013 while retaining the architectural details that give it its personality. A metal roof was added in 2020, and the back exterior steps were replaced in 2023. Adding to the convenience, this unit comes with two dedicated deeded parking spaces--a particularly valuable feature for downtown living. With its generous size, historic character, flexible living spaces, downtown views, and location directly on Main Street, this is a rare opportunity to own something you simply don't see come along very often in the surrounding area. Currently operated as a short-term rental, the property offers an established opportunity for someone looking to continue that use, while also being equally well suited as a primary residence or a weekend retreat. A home with history, space, and a front-row seat to downtown Jonesborough. Buyer(s)/buyer(s) agent to verify all information.